Coaching startup founders is a high-stakes, high-impact discipline that requires sharp psychological insight, real-world business acumen, and the ability to balance challenge with support.

Our approach is based on Rich Hagberg’s 45 years of coaching executives.  For the last 16 years he has been focused on startup founders, working with close to 200 founders.  His research what makes a founder a founder and what it takes to scale founder’s leadership capabilities has been described in detail in “Founders Keepers”. 

Founders have unique strengths and weaknesses which can be assets in scrappy startup, with a style that helps get their company off the ground.  However, many of these same traits can prevent them from adapting to more complex and sophisticated organizational challenges when a company gets larger. They hit their ceiling.  

Founders also can be difficult to coach.  We provide unique techniques that help the founder coach navigate this challenging task.  Founders can be narcissistic, autocratic, lone-wolf control-freaks who are sometimes called “genius jerks”. .  They are often stressed and burned out and feel they don’t have time for coaching until they realize that they have hit the wall. Many hide their insecurity and fear that they are an imposter by presenting a façade of confidence, making them less willing to acknowledge their own shortcomings.  They fear letting go of control and micromanage and disempower their teams.  

Founders are also data-driven, focused on results and tend to respect numbers, performance metrics and concrete outcomes. Coaching founders requires the ability to deliver tough feedback that shows them how their behavior is impacting their success and causing issues.  Using performance metrics and employee feedback provided by 360 ratings shows them how their actions affect their team, productivity and customer retention.

Founders need coaching that both challenges them and helps them solve the continuous problems they face.  The coach needs to be able to help them think through their challenges, push them out of their comfort zones but also be their supportive ally.  They feel isolated at the top, drained by fatigue and stress and in need of someone they can trust, who has empathy for their problems. Founders welcome direct feedback but need to feel that you are in their corner helping them achieve their goals and showing that you understand their pressure, their vision.  You need to push them without triggering resistance.

Many founders are inexperienced and need a coach who can help them manage a growing company by offering them best practice insights that can fill their knowledge gaps.  Bring in proven frameworks, tools, and processes from other successful startups or industries. Founders will appreciate practical, actionable advice that helps them streamline their operations or improve leadership. Whether it’s about hiring, team dynamics, or financial management, providing best practices gives them a solid foundation to build upon.

Some are visionary and creative, while others are highly technical or deeply analytical. Some are extroverted and thrive on building relationships, while others prefer to stay behind the scenes and focus on product development. Effective coaching means adjusting your approach to meet the specific needs and personality of the founder. A coach must tailor your coaching style to the founder’s strengths, weaknesses, and leadership style. For highly creative founders, you might need to bring more structure and focus to the conversation, while for analytical founders, you may need to help them develop emotional intelligence and communication skills.

Founders are often driven by a mix of conscious ambitions (such as scaling their company or becoming an industry leader) and unconscious motivations (such as the need for control, fear of failure, or desire for recognition). To coach a founder effectively, you need to tap into both of these layers and understand what’s driving their behavior by asking probing questions that get to the heart of their motivations and understand their underlying fears and desires.